Potassium Hydroxide → 4-(4-Methyl-1h-imidazol-1-yl)benzenamine

HRID 472160

반응식

HRID 472160 반응식
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)[CH:6]=1.O.O.Cl[Sn]Cl.[OH-].[K+]>C(O)C>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[CH:6]=1

참가 물질

5

반응물 3

HCID 14797Potassium Hydroxide2회HCID 61436Stannous chloride dihydrateHCID 160051694-Methyl-1-(4-nitrophenyl)-1H-imidazole

생성물 1

HCID 160051704-(4-Methyl-1h-imidazol-1-yl)benzenamine수율 10,152.9%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
0 °C

실험 절차

4-(4-methyl-1H-imidazol-1-yl)nitrobenzene (22.5 g; 0.87 mmol) is dissolved in abs. ethanol (250 mL), then SnCl2.2H2O (125 g; 0.55 mol) is added portion-wise, on cooling at 0° C. The resulting mixture is stirred at r.t. for 2 hours and heated at reflux overnight. The reaction mixture is then cooled at r.t. and the pH is adjusted to 12, by adding 30% KOH (500 mL), then KOH pellets under stirring. The resulting suspension is filtered and the cake is washed with ethanol, the combined filtrate and washings are concentrated and the residue is extracted with DCM. Concentration of the combined organic extracts afforded the title product as a slight brown solid (15.3 g; 80%), m.p.: 122-125° C. C10H11N3, MW 173.22.

후처리

  1. temperatureheated
  2. temperatureat reflux overnight
  3. temperatureThe reaction mixture is then cooled at r.t.
  4. filtrationThe resulting suspension is filtered
  5. washthe cake is washed with ethanol
  6. concentrationthe combined filtrate and washings are concentrated
  7. extractionthe residue is extracted with DCM

출처 및 근거

ORD 기록
ord-38007aa131cc43e6ac40724e0553f5da
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633208B2

연결된 노트

불러오는 중…